4,5-dimethyl-2,6-bis(4-methylphenyl)pyrimidine | 256482-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,5-dimethyl-2,6-bis(4-methylphenyl)pyrimidine
• 英文别名: 4,5-Dimethyl-2,6-bis(4-methylphenyl)pyrimidine
• CAS: 256482-06-1
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: KLGYVMZMRCACHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Os(hydride)6(triisopropylphosphine)2 、 4,5-dimethyl-2,6-bis(4-methylphenyl)pyrimidine 以 甲苯 为溶剂， 以25%的产率得到[OsH3(4,5-dimethyl-2,6-bis(4-methylphenyl)pyrimidine(-H))(P(iPr)3)2]
  参考文献：
  名称：

  Multiple C−H Bond Activation of Phenyl-Substituted Pyrimidines and Triazines Promoted by an Osmium Polyhydride: Formation of Osmapolycycles with Three, Five, and Eight Fused Rings

  摘要：

  The reactions of the hexahydride complex OsH6((PPr3)-Pr-i)(2) (1) with 4,5-dimethyl-2,6-bis(4-methlylphenyl)-pyrimidine (H(2)L1), 2,4,6-tris-(4-methylphenyl)-1,3,5-triazine (H(4)L2), and 2,4,6-triphenylpyrimidine (H(4)L3) have been studied. Complex 1 reacts with H(2)L1 to give a mixture of the metallapolycyclic derivatives OsH3(HL1)((PPr3)-Pr-i)(2) (2) and OsH2(L1)((PPr3)-Pr-i)(2) (3). Compound 2 arises from the coordination of the N3-pyrimidine nitrogen atom to osmium and the ortho-CH bond activation of the C2-bonded phenyl group. The formation of 3 involves the coordination of the N1-pyrimidine nitrogen atom to osmium and the ortho-CH bond activation of both phenyl groups. The reaction of 1 with H4L2 leads to a mixture of OsH2(H2L2)((PPr3)-Pr-i)(2) (4) and ((PPr3)-Pr-i)(2)H2Os-(L-2)OsH2((PPr3)-Pr-i)(2) (5), containing five and eight fused rings, respectively. Complex 4 results from the coordination of the NI -triazine nitrogen atom to osmium and the ortho-CH bond activation of the phenyl groups at positions 2 and 6 of the triazine ring. Complex 5 results from the coordination of the NI and N3 of triazine to two different metal centersalong with a double ortho-CH bond activation in each proximal phenyl group. Complex 1 reacts with H4L3 to afford OsH2(H2L3)((PPr3)-Pr-i)(2) (6) and ((PPr3)-Pr-i)(2)H2Os(L3)OsH2((PPr3)-Pr-i)(2) (7), which are related to 4 and 5, respectively. Complexes 2, 3,4, and 5 have been characterized by X-ray diffraction analysis. The structures prove the plananty of their cores and suggest clectron delocalization through the polycyclic system. Quantum chemical calculations (DFT level) on model Compounds clearly indicate that the Os-C and Os-N bonds of the newly formed metallapolycycles exhibit a remarkable double-bond character that is higher for the Os-C bond, in very good agreement with the experimental findings.

  DOI：

  10.1021/om901030q

文献信息

• Multiple C−H Bond Activation of Phenyl-Substituted Pyrimidines and Triazines Promoted by an Osmium Polyhydride: Formation of Osmapolycycles with Three, Five, and Eight Fused Rings
  作者：Miguel A. Esteruelas、Israel Fernández、Antonio Herrera、Mamen Martín-Ortiz、Roberto Martínez-Álvarez、Montserrat Oliván、Enrique Oñate、Miguel A. Sierra、Marta Valencia

  DOI：10.1021/om901030q

  日期：2010.2.22

  The reactions of the hexahydride complex OsH6((PPr3)-Pr-i)(2) (1) with 4,5-dimethyl-2,6-bis(4-methlylphenyl)-pyrimidine (H(2)L1), 2,4,6-tris-(4-methylphenyl)-1,3,5-triazine (H(4)L2), and 2,4,6-triphenylpyrimidine (H(4)L3) have been studied. Complex 1 reacts with H(2)L1 to give a mixture of the metallapolycyclic derivatives OsH3(HL1)((PPr3)-Pr-i)(2) (2) and OsH2(L1)((PPr3)-Pr-i)(2) (3). Compound 2 arises from the coordination of the N3-pyrimidine nitrogen atom to osmium and the ortho-CH bond activation of the C2-bonded phenyl group. The formation of 3 involves the coordination of the N1-pyrimidine nitrogen atom to osmium and the ortho-CH bond activation of both phenyl groups. The reaction of 1 with H4L2 leads to a mixture of OsH2(H2L2)((PPr3)-Pr-i)(2) (4) and ((PPr3)-Pr-i)(2)H2Os-(L-2)OsH2((PPr3)-Pr-i)(2) (5), containing five and eight fused rings, respectively. Complex 4 results from the coordination of the NI -triazine nitrogen atom to osmium and the ortho-CH bond activation of the phenyl groups at positions 2 and 6 of the triazine ring. Complex 5 results from the coordination of the NI and N3 of triazine to two different metal centersalong with a double ortho-CH bond activation in each proximal phenyl group. Complex 1 reacts with H4L3 to afford OsH2(H2L3)((PPr3)-Pr-i)(2) (6) and ((PPr3)-Pr-i)(2)H2Os(L3)OsH2((PPr3)-Pr-i)(2) (7), which are related to 4 and 5, respectively. Complexes 2, 3,4, and 5 have been characterized by X-ray diffraction analysis. The structures prove the plananty of their cores and suggest clectron delocalization through the polycyclic system. Quantum chemical calculations (DFT level) on model Compounds clearly indicate that the Os-C and Os-N bonds of the newly formed metallapolycycles exhibit a remarkable double-bond character that is higher for the Os-C bond, in very good agreement with the experimental findings.